Micelle Formation and Its Relationship to Solubility Behavior of 2-Butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl Ketone Hydrochloride

Micelle formation by 2-butyl-3-benzofuranyl-4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl ketone hydrochloride was studied by conductance measurements. The CMC was approximately 0.05% and was independent of temperature between 20 and 50°. The heat of formation for the micelle was calculated to be 6.9 kcal/mole. The unusual solubility behavior of the compound was attributed to its ability to form micelles. Ultracentrifuge studies indicate the molecular weight of the micelle to be approximately 100,000. Anions such as chloride, sulfate, acetate, tartrate, and citrate significantly affect the equilibrium solubility of the compound. NMR spectroscopic data indicate that the solubility behavior, in part, is related to an effect on the CMC of the compound by the anionic environment.